Hydrochloric Acid → 2-{4-(2-({(2-(4-Chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(pyrrolidin-1-yl)pyridin-4-yl)phenoxy}ethyl L-lysyl-L-alaninate dihydrochloride

HRID 1968339Notes

Reaction equation

HRID 1968339 reaction equation
C(OC([NH:8][C@H:9]([C:22]([NH:24][C@H:25]([C:27]([O:29][CH2:30][CH2:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[C:44]([C:45]#[N:46])=[C:43]([N:47]3[CH2:51][CH2:50][CH2:49][CH2:48]3)[N:42]=[C:41]([S:52][CH2:53][C:54]3[N:55]=[C:56]([C:59]4[CH:64]=[CH:63][C:62]([Cl:65])=[CH:61][CH:60]=4)[S:57][CH:58]=3)[C:40]=2[C:66]#[N:67])=[CH:35][CH:34]=1)=[O:28])[CH3:26])=[O:23])[CH2:10][CH2:11][CH2:12][CH2:13][NH:14]C(OC(C)(C)C)=O)=O)(C)(C)C.[ClH:68]>ClCCl.C(OCC)C>[ClH:65].[ClH:68].[NH2:8][C@H:9]([C:22]([NH:24][C@H:25]([C:27]([O:29][CH2:30][CH2:31][O:32][C:33]1[CH:34]=[CH:35][C:36]([C:39]2[C:44]([C:45]#[N:46])=[C:43]([N:47]3[CH2:48][CH2:49][CH2:50][CH2:51]3)[N:42]=[C:41]([S:52][CH2:53][C:54]3[N:55]=[C:56]([C:59]4[CH:64]=[CH:63][C:62]([Cl:65])=[CH:61][CH:60]=4)[S:57][CH:58]=3)[C:40]=2[C:66]#[N:67])=[CH:37][CH:38]=1)=[O:28])[CH3:26])=[O:23])[CH2:10][CH2:11][CH2:12][CH2:13][NH2:14]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 866438502-{4-(2-({(2-(4-Chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(pyrrolidin-1-yl)pyridin-4-yl)phenoxy}ethyl N2,N6-bis(tert-butoxycarbonyl)-L-lysyl-L-alaninate

Product 1

HCID 687649662-{4-(2-({(2-(4-Chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(pyrrolidin-1-yl)pyridin-4-yl)phenoxy}ethyl L-lysyl-L-alaninate dihydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

300 mg (0.308 mmol) of 2-{4-(2-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(pyrrolidin-1-yl)pyridin-4-yl)phenoxy}ethyl N2,N6-bis(tert-butoxycarbonyl)-L-lysyl-L-alaninate (Example 26A) were initially charged in 5.4 ml of dichloromethane. 3.08 ml (6.163 mmol) of a 1N solution of hydrogen chloride in diethyl ether were added, and the reaction solution was then stirred at RT overnight. The solid formed was filtered off, triturated with 2.5 ml of cold dichloromethane and filtered off again. This gave 250 mg (96% of theory) of the target compound.

Workup

  1. customThe solid formed
  2. filtrationwas filtered off
  3. customtriturated with 2.5 ml of cold dichloromethane
  4. filtrationfiltered off again

Sources & evidence

ORD record
ord-e1f1e8ec777f444c90b3bbb0faddc0d5
Source dataset
uspto-grants-2013_04
Patent number
US08420825B2

Reaction notes

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